JP5411927B2 - Ｃｃｒ１アンタゴニストとしてのピラゾール化合物 - Google Patents
Ｃｃｒ１アンタゴニストとしてのピラゾール化合物 Download PDFInfo
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- JP5411927B2 JP5411927B2 JP2011508559A JP2011508559A JP5411927B2 JP 5411927 B2 JP5411927 B2 JP 5411927B2 JP 2011508559 A JP2011508559 A JP 2011508559A JP 2011508559 A JP2011508559 A JP 2011508559A JP 5411927 B2 JP5411927 B2 JP 5411927B2
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- Prior art keywords
- alkyl
- phenyl
- methyl
- mmol
- alkoxy
- Prior art date
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- 239000005557 antagonist Substances 0.000 title description 10
- 102100031172 C-C chemokine receptor type 1 Human genes 0.000 title description 2
- 101710149814 C-C chemokine receptor type 1 Proteins 0.000 title description 2
- 150000003217 pyrazoles Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 115
- 150000001875 compounds Chemical class 0.000 claims description 75
- -1 4-methylpiperidin-1-ylcarbonyl Chemical group 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 201000006417 multiple sclerosis Diseases 0.000 claims description 15
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
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- 150000002367 halogens Chemical class 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 208000037976 chronic inflammation Diseases 0.000 claims description 8
- 230000006020 chronic inflammation Effects 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
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- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
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- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims description 2
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- 206010049567 Miller Fisher syndrome Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 206010040047 Sepsis Diseases 0.000 claims description 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 208000026935 allergic disease Diseases 0.000 claims description 2
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- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 2
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- 206010009887 colitis Diseases 0.000 claims description 2
- 208000010247 contact dermatitis Diseases 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 2
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- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 2
- 206010064539 Autoimmune myocarditis Diseases 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
- 239000000243 solution Substances 0.000 description 68
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- 235000019439 ethyl acetate Nutrition 0.000 description 36
- 239000000203 mixture Substances 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 238000000034 method Methods 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 239000007787 solid Substances 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 18
- 239000000460 chlorine Substances 0.000 description 18
- 229920006395 saturated elastomer Polymers 0.000 description 18
- 239000012267 brine Substances 0.000 description 17
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- 238000003818 flash chromatography Methods 0.000 description 15
- 229910052938 sodium sulfate Inorganic materials 0.000 description 15
- 235000011152 sodium sulphate Nutrition 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 102000000013 Chemokine CCL3 Human genes 0.000 description 11
- 239000000654 additive Substances 0.000 description 11
- 229910052717 sulfur Chemical group 0.000 description 11
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- 239000002253 acid Substances 0.000 description 10
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- 229910052757 nitrogen Inorganic materials 0.000 description 10
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- 238000004007 reversed phase HPLC Methods 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 6
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- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 6
- OAPQKGGVDCZENK-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-methylpyrazole-4-carboxylic acid Chemical compound CC1=C(C(O)=O)C=NN1C1=CC=C(Cl)C=C1 OAPQKGGVDCZENK-UHFFFAOYSA-N 0.000 description 5
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
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- YICFALDKKMHFLT-UHFFFAOYSA-M sodium;3-methoxy-3-oxopropane-1-sulfinate Chemical compound [Na+].COC(=O)CCS([O-])=O YICFALDKKMHFLT-UHFFFAOYSA-M 0.000 description 1
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- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Transplantation (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5069308P | 2008-05-06 | 2008-05-06 | |
| US61/050,693 | 2008-05-06 | ||
| PCT/US2009/042455 WO2009137338A1 (fr) | 2008-05-06 | 2009-05-01 | Composés de pyrazole comme antagonistes de ccr1 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011520806A JP2011520806A (ja) | 2011-07-21 |
| JP5411927B2 true JP5411927B2 (ja) | 2014-02-12 |
Family
ID=40801863
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011508559A Active JP5411927B2 (ja) | 2008-05-06 | 2009-05-01 | Ｃｃｒ１アンタゴニストとしてのピラゾール化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8293917B2 (fr) |
| EP (1) | EP2297112B1 (fr) |
| JP (1) | JP5411927B2 (fr) |
| CA (1) | CA2722811C (fr) |
| WO (1) | WO2009137338A1 (fr) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009134666A1 (fr) | 2008-04-29 | 2009-11-05 | Boehringer Ingelheim International Gmbh | Composés indazole comme antagonistes des récepteurs ccr1 |
| CA2722811C (fr) | 2008-05-06 | 2016-07-05 | Boehringer Ingelheim International Gmbh | Composes de pyrazole comme antagonistes de ccr1 |
| AU2009296839A1 (en) | 2008-09-26 | 2010-04-01 | Boehringer Ingelheim International Gmbh | Azaindazole compounds as CCR1 receptor antagonists |
| US8946231B2 (en) * | 2009-03-23 | 2015-02-03 | Merck Sharp & Dohme Corp. | P2X3, receptor antagonists for treatment of pain |
| NZ599132A (en) | 2009-10-21 | 2014-05-30 | Boehringer Ingelheim Int | Indazole and pyrazolopyridine compounds as ccr1 receptor antagonists |
| EP2493875B1 (fr) | 2009-10-27 | 2014-08-06 | Boehringer Ingelheim International GmbH | Composés hétérocycliques utilisés en tant qu'antagonistes des récepteurs ccr1 |
| CN102596908A (zh) * | 2009-12-08 | 2012-07-18 | 贝林格尔.英格海姆国际有限公司 | 用于制备取代的吲唑和氮杂吲唑化合物的中间体的合成方法 |
| AP3360A (en) * | 2010-01-27 | 2015-07-31 | Boehringer Ingelheim Int | Pyrazole compounds as CRTH2 antagonists |
| EP2563787B1 (fr) | 2010-04-30 | 2014-11-26 | Boehringer Ingelheim International GmbH | Composés azaindazole amides en tant qu'antagonistes des récepteurs ccr1 |
| ES2610185T3 (es) * | 2010-09-21 | 2017-04-26 | Eisai R&D Management Co., Ltd. | Composición farmacéutica |
| EP2655371B1 (fr) | 2010-12-23 | 2015-02-25 | Boehringer Ingelheim International GmbH | Composés de pyrazolopipéridine en tant qu'antagonistes de récepteur ccr1 |
| WO2012103071A2 (fr) * | 2011-01-25 | 2012-08-02 | Eisai R&D Management Co., Ltd. | Composés et compositions |
| WO2012163848A1 (fr) | 2011-05-27 | 2012-12-06 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Procédés et compositions pharmaceutiques destinés au traitement de la maladie de crohn |
| PL2736888T3 (pl) | 2011-07-26 | 2016-04-29 | Sanofi Sa | Pochodne kwasu 3-heteroaroiloamino-propionowego i ich zastosowanie jako środków farmaceutycznych |
| CA2852160A1 (fr) | 2011-10-28 | 2013-05-02 | Galderma Research & Development | Nouveaux marqueurs d'infiltrat leucocytaire de rosacee et utilisations de ceux-ci |
| EP2871179A4 (fr) | 2012-07-03 | 2016-03-16 | Ono Pharmaceutical Co | Composé ayant une activité agoniste sur un récepteur de la somatostatine, et leur utilisation à des fins médicales |
| CA2893597C (fr) | 2012-12-07 | 2021-06-29 | Chemocentryx, Inc. | Lactames de diazole |
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| Publication number | Publication date |
|---|---|
| US20110230521A1 (en) | 2011-09-22 |
| JP2011520806A (ja) | 2011-07-21 |
| CA2722811C (fr) | 2016-07-05 |
| WO2009137338A1 (fr) | 2009-11-12 |
| EP2297112B1 (fr) | 2013-04-03 |
| EP2297112A1 (fr) | 2011-03-23 |
| CA2722811A1 (fr) | 2009-11-12 |
| US8293917B2 (en) | 2012-10-23 |
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